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Issue 26, 2015
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Transition-metal-catalyzed intramolecular cyclization of amido(hetero)arylboronic acid aldehydes to isoquinolinones and derivatives

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Abstract

We report an innovative and simple three step high yielding synthesis of a library of 14 chiral isoquinolinone and azepinone derivatives with benzyl, pyridyl and thiophene cores starting from amidoarylboronic acid aldehydes. These products have potential for treating neurodegenerative diseases. The key reaction in this synthetic pathway was an efficient metal-catalyzed (with Rh, Cu and Pd catalysts) intramolecular cyclization. A maximum yield of 87% was obtained using a Rh(I) catalyst.

Graphical abstract: Transition-metal-catalyzed intramolecular cyclization of amido(hetero)arylboronic acid aldehydes to isoquinolinones and derivatives

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Article information


Submitted
08 Jan 2015
Accepted
09 Feb 2015
First published
09 Feb 2015

RSC Adv., 2015,5, 20108-20114
Article type
Communication

Transition-metal-catalyzed intramolecular cyclization of amido(hetero)arylboronic acid aldehydes to isoquinolinones and derivatives

C. S. Marques, D. Peixoto and A. J. Burke, RSC Adv., 2015, 5, 20108
DOI: 10.1039/C5RA00404G

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